DEVELOMMENT OF NEW AZIRIDINYL SUBSTITUTED PHOSPHONIC ACID ORGANOCATALYTS FOR THE ENANTIOSELECTIVE ADDITION OF INDOLES TO NITROOLEFINES

2017-12-31
DEVELOMMENT OF NEW AZIRIDINYL SUBSTITUTED PHOSPHONIC ACID ORGANOCATALYTS FOR THE ENANTIOSELECTIVE ADDITION OF INDOLES TO NITROOLEFINES

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Homoconjugated and Spiro Push-Pull Systems: Cycloadditions of Naphtho- and Anthradiquinones with Electron-Rich Alkynes
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We report the synthesis and characterization of three new classes of push-pull chromophores using [2+2]-cycloaddition reactions of electron-rich alkynes and electron-poor alkenes. Previous investigations have focused on the reactions of cyano-substituted electron acceptors. This study demonstrates that cyano-free electron acceptors, naphtho- and anthradiquinones, can also be used to access extended push-pull systems. The effects of the structural changes on the spectroscopic and electronic properties were i...
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The chemoenzymatic synthesis of both of the enantiomers of pharmacologically interesting compounds such as 4,5,6,7-tetrahydro-4-oxobenzofuran-5-yl acetate (2a), 4,5,6,7-tetrahydro-4-oxo-6,6-dimethylbenzofuran-5-yl acetate (2b), and their hydroxy derivatives 3a, 3b, 1-benzyl4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate (5), starting from 6,7-dihydrobenzofuran-4(5H)-one (la), 6,7-dihydro-6,6-dimethylbenzofuran4(5H)-one (7b), and 1-benzyl-6,7-dihydro-1 H-indol-4(5H)-one (4) are reported. Manganese(III) acet...
Diethylzinc mediated 1 3 dipolar cycloaddition reaction of chiral azomethine ylides asymmetric synthesis of ferrocenyl substituted pyrrolidine derivatives
Doğan, Özdemir; DİNÇER, Ülkü; ARICI, Cengiz (2002-10-01)
Asymmetric synthesis of ferrocenyl-substituted pyrrolidine derivatives was successfully achieved by diethylzinc-mediated 1,3-dipolar cycloaddition reactions of chiral azomethine ylides with a number of electron-deficient dipolarophiles. Chiral azomethine ylides were formed by condensing glycyl sultam with ferrocenecarboxaldehyde via imine tautomerization and complexation with diethylzinc. All of the cycloaddition reactions gave ferrocenyl-substituted pyrrolidine derivatives with very high regio- and diaster...
Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs
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Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective reduction of the C-N bond followed by separation of the formed diastereoisomers, furnished (2-arylcy...
Citation Formats
Ö. Doğan, “DEVELOMMENT OF NEW AZIRIDINYL SUBSTITUTED PHOSPHONIC ACID ORGANOCATALYTS FOR THE ENANTIOSELECTIVE ADDITION OF INDOLES TO NITROOLEFINES,” 2017. Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/61209.